Phosphorus oxychloride → 4-Chloro-7-methoxyquinoline

HRID 1925367Notes

Reaction equation

HRID 1925367 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12](O)=[CH:13][CH:14]=[N:15]2)=[CH:10][CH:9]=1>>[Cl:3][C:12]1[C:11]2[C:16](=[CH:17][C:8]([O:7][CH3:6])=[CH:9][CH:10]=2)[N:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178487715HCID 178487715, compound

Product 1

HCID 106078294-Chloro-7-methoxyquinoline

Procedure

To a solution of POCl3 (11 mL, excess), 7-methoxyquinolin-4-ol (1.87 g, 10.67 mmol) was added and heated from RT to 90° C. The mixture was allowed to cool to RT, concentrated in-vacuo and cooled in an ice bath during the slow adjustment to pH 7 by alternating ice and 1N NaOH. The solid was filtered and rinsed with water. The title compound was isolated as a tan solid.

Workup

  1. temperatureheated from RT to 90° C
  2. concentrationconcentrated in-vacuo
  3. temperaturecooled in an ice bath during the slow adjustment to pH 7
  4. filtrationThe solid was filtered
  5. washrinsed with water

Sources & evidence

ORD record
ord-ae5a4c22a4aa4ea98bb09e434a443bff
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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